The paper presents a comparative legal and comparative historical analysis of one of the aspects of the institution of the arbitration, namely, the election of an arbitrator. The contractual, non-state nature of arbitration leaves the disputing parties with a wide freedom of expression, including in determining the personality of a mediator or intermediaries in resolving a dispute. The paper focuses on identifying the key features that the disputing parties should pay attention to when choosing an arbitrator (judges). The Roman jurists established comprehensive and justified set of personality traits that an arbitrator should possess in order to maintain the general idea of the conclusiveness of judicial decisions. According to the norms of Roman law, an arbitrator must be a free person, physically healthy, with a developed intellect, with life experience, not tainted by immoral acts, not involved in illegal activities, not interested in a certain outcome of the case. In the Middle Ages, the system of mandatory requirements for a mediator in a dispute was reduced due to the simplification of public relations regulated by customary law, which was reflected in legislative documents. Priority was given to the high social stratum, ethnic and religious conformity of the judge to the disputing persons. In modern times, the freedom of litigants to choose arbitrators is almost absolute, taking into account the tendency to individualize the interests of the parties to the conflict and the inability to take into account all the particular circumstances of various disputes that could affect the choice of an arbitrator. Only when resolving economic disputes, the parties were guided by the judge’s special knowledge, which makes it possible to understand the essence of the property dispute and make a fair decision. The analysis made it possible to identify the continuity of the provisions of Roman law and the requirements imposed on the arbitration intermediary in the Middle Ages and Modern times. Historical comparison revealed a tendency to reduce the number of mandatory features of the candidate for arbitration, which determined the growing importance of the freedom of the disputing parties as the most significant feature of the arbitration court.